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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1174000Generated: October 26, 2026

(3-Cyanopropyl)triphenylphosphonium bromide → 5-[6-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-quinolin-2-yl]-penta-4-ennitrile

https://huagongshe.com/reaction/1174000

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(3-Cyanopropyl)triphenylphosphonium bromideHCID 3036619—
Reactant3-[6-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-quinolin-2-yl]-propionitrileHCID 21084402—
ReactantLDA heptaneHCID 86599834—
SolventTetrahydrofuranHCID 8028—
Product5-[6-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-quinolin-2-yl]-penta-4-ennitrileHCID 6694184875.9%

Reaction Steps

The compound (675.0 mg) obtained in Example 123-1 was suspended in anhydrous THF (30 ml) and cooled with ice. Then, the suspension was added with a 2 mol/l lithium diisopropylamide/heptane solution (0.825 ml), followed by stirring at room temperature for 1 hour. Then, the solution was gradually added with a solution prepared by suspending the compound (327.9 mg) obtained in Example 119-7 in anhydrous THF (20 ml), followed by stirring at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (268.0 mg) as a yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07833991B2
Source datasetuspto-grants-2010_11
ORD IDord-b44bcb75316b47279e7c895031b81fea
Source noteuspto-grants-2010_11